5-thioacetoxypentyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl dimer

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 5-thioacetoxypentyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl dimer
• 英文别名: 5,5'-dithiobis(pentyl α-D-mannopyranoside)；(2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-[5-[5-[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxypentyldisulfanyl]pentoxy]oxane-3,4,5-triol
• 化学式: C₂₂H₄₂O₁₂S₂
• 分子量: 562.7
• InChiKey: HGKUNGNEOYANBU-FUVCNDBXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.5
• 重原子数：
  36
• 可旋转键数：
  17
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  249
• 氢给体数：
  8
• 氢受体数：
  14

反应信息

• 作为产物：
  描述：

  2,3,4,6-四-O-乙酰基-1-溴-Alpha-D-甘露糖 在 甲醇 、 calcium sulfate 、 偶氮二异丁腈 、 sodium methylate 、 氰化汞 、 硫代乙酸 作用下， 以 1,4-二氧六环 、 甲苯 、 乙腈 为溶剂， 反应 6.5h， 生成 5-thioacetoxypentyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl dimer
  参考文献：
  名称：

  Selective Binding of Mannose-Encapsulated Gold Nanoparticles to Type 1 Pili in Escherichia coli

  摘要：

  The synthesis, characterization and biological application of mannose encapsulated gold nanoparticles (m-AuNP) are reported. m-AuNP is well dispersed and very stable without aggregation in the media of broad ion strength and pH ranges. The selective binding of m-AuNP to the mannose adhesin FimH of bacterial type 1 pili is demonstrated using transmission electron microscopy. The competition assay with free mannose suggests that m-AuNP binds FimH better than free mannose does. This work demonstrates that carbohydrate attached nanoparticles can be used as an efficient affinity label and a multi-ligand carrier in a biological system.

  DOI：

  10.1021/ja0200903

文献信息

• Gold<i>Manno</i>-Glyconanoparticles: Multivalent Systems to Block HIV-1 gp120 Binding to the Lectin DC-SIGN
  作者：Olga Martínez-Ávila、Karolin Hijazi、Marco Marradi、Caroline Clavel、Colin Campion、Charles Kelly、Soledad Penadés

  DOI：10.1002/chem.200900923

  日期：2009.9.28

  ending in thiol groups, which enable attachment of the glycoconjugates to the gold surface, have been prepared. manno‐GNPs with different spacers and variable density of mannose (oligo)saccharides have been obtained and characterized. Surface plasmon resonance (SPR) experiments with selected manno‐GNPs have been performed to study their inhibition potency towards DC‐SIGN binding to gp120. The tested manno‐GNPs

  HIV包膜糖蛋白gp120利用其表面的高甘露糖簇将树突状细胞靶向C型凝集素树突状细胞特异的细胞内粘附分子-3夺取非整联蛋白（DC‐SIGN）。模仿寡聚甘露糖苷在病毒表面的簇状存在是设计基于碳水化合物的抗病毒剂的一种策略。受gp120簇呈递的生物启发，我们设计并准备了一个小型多价水溶性金糖纳米颗粒（manno- GNP）库，其展示了高甘露糖十一碳糖Man 9 GlcNAc 2的截短的（寡聚）甘露糖苷。并测试了它们作为DC-SIGN与gp120结合的抑制剂。这些糖纳米颗粒是DC-SIGN的配体，DC-SIGN还可在感染的早期阶段通过对相关聚糖的特异性识别而与大量病原体相互作用。制备了具有以硫醇基结尾的不同间隔基的（寡）甘露糖苷，其使得糖缀合物能够附着至金表面。低聚甘露已经获得和表征具有不同间隔和甘露糖（低聚）糖的可变密度的GNP。已经进行了使用选定的甘露糖-GNP的表面等离振子共振（SPR）实
• Selective Binding of Mannose-Encapsulated Gold Nanoparticles to Type 1 Pili in <i>Escherichia coli</i>
  作者：Chun-Cheng Lin、Yi-Chun Yeh、Chan-Yi Yang、Chan-Long Chen、Gee-Fong Chen、Chia-Chun Chen、Yi-Chun Wu

  DOI：10.1021/ja0200903

  日期：2002.4.1

  The synthesis, characterization and biological application of mannose encapsulated gold nanoparticles (m-AuNP) are reported. m-AuNP is well dispersed and very stable without aggregation in the media of broad ion strength and pH ranges. The selective binding of m-AuNP to the mannose adhesin FimH of bacterial type 1 pili is demonstrated using transmission electron microscopy. The competition assay with free mannose suggests that m-AuNP binds FimH better than free mannose does. This work demonstrates that carbohydrate attached nanoparticles can be used as an efficient affinity label and a multi-ligand carrier in a biological system.